| 7. Round | 03/08/2008 | Deportes Melipilla | - | Provincial Osorno (old) | 3:1 |  |
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| 9. Round | 17/08/2008 | Provincial Osorno (old) | - | Cobresal | 0:3 | ||||
| 10. Round | 23/08/2008 | Audax Italiano | - | Provincial Osorno (old) | 1:2 | ||||
| 11. Round | 31/08/2008 | Provincial Osorno (old) | - | Universidad de Chile | 1:2 | ||||
| 17. Round | 25/10/2008 | Palestino | - | Provincial Osorno (old) | 1:0 | ||||
| 19. Round | 09/11/2008 | Provincial Osorno (old) | - | Unión Española | 1:2 |
Chile